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Vacation rentals with a kayak in Sarasota

Find and book unique kayak rentals on Airbnb

Top-rated kayak rentals in Sarasota

Guests agree: these kayak rentals are highly rated for location, cleanliness, and more.

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Home in Longboat Key

4.86 out of 5 average rating, 110 reviews

Summer House longboat key

Luxurious waterfront 3 Bedroom home with bay and and canal view with extra dock that can accommodate up to 21 ft+-heated pool, tropical landscaping with coconut palms, outside patio and grill. Fish on the dock and watch dolphins and manatee. Truly a tropical paradise just 7 minute Walk to your own private beach, It is a private home nestled on a canal that is 2 houses from Sarasota Bay. Our home is situated in the desirable quiet neighborhood of Country Club Shore minutes from at Armand’s circle

Home in Bradenton

4.97 out of 5 average rating, 109 reviews

WOW-King Bed w/86° Pool, Turf Golf green, Beaches

Location!! Have fun with the whole family at this stylish home. Just minutes to Anna Maria Island beaches. This incredible newly built home sets the highest standards of luxury living. It’s the ideal retreat with its expansive views of the outdoors from the moment you enter. Open concept with large French doors throughout the home creates the perfect indoor-outdoor lifestyle. Spend the day lounging by the heated pool with a cold drink in your hand. Fun turf yard area with games and putting green

Guest suite in Sarasota

4.94 out of 5 average rating, 503 reviews

Studio Apartment. Priv Yard. 5 min to Siesta Key!

Self checkin. Includes kayak and bikes! You’ll love my place because of the coziness, the high ceilings, and the location. My place is good for couples, solo adventurers, and business travelers. Converted garage space. Your own private fenced back yard, kitchenette, fridge, private bathroom, Amazon Firestick with Netflix, Hulu and dock/boat ramp just 30 sec from your door and in a beautiful neighborhood. Just a 10 min bike ride to Siesta Key. The #1 beach in America! What more could you ask for!

Cottage in Englewood

4.88 out of 5 average rating, 133 reviews

Free bikes/kayaks/walk to beach/2bed/2bath #2

Unit # 2 Beautiful 2 bed 2 bath cottage, great space to relax with family and friends. With full kitchen/ garage/laundry/outdoor shower. WiFi/Free bikes, kayaks, beach toys. Great Lanai to spend wonderful afternoons. You will love to walk to the beach and enjoy the most breathtaking sunset pictures. This cottage is fully furnished beach style for a wonderful vacation feeling. You have not only the beach and the bay to explore, but great restaurants/bars and more just walking distance. Enjoy!

Tiny home in Sarasota

4.96 out of 5 average rating, 310 reviews

@Shellmateisland |tiny home| island| bikes| kayaks

⭑Octagonal 320ft² tiny home sitting on a private 1.5-acre island!⭑ ✯ Lake access ✯ Walk to dining, nightlife, and shopping ✯ Fully equipped + stocked kitchen ✯ Free bikes + kayaks +beach gear ✯ Backyard fire pit + BBQ ✯ Screened-in outdoor lounge w/ hammocks ✯ Smart TV w/ Netflix ✯ Memory foam bed ✯ 426Mbps wifi Ask which fruit trees are in season for a homegrown treat! 3 min → Siesta Key Beach 7 min → Downtown SRQ 12 min → Myakka River State Park (river kayaking + wildlife viewing)

Guest suite in Englewood

4.98 out of 5 average rating, 187 reviews

Blue Cottage Suite- Peaceful Old Englewood Charm!

This charming rental is in historic Old Englewood right at the edge of Lemon Bay. The Blue Cottage is in a quiet neighborhood just 4 blocks from Dearborn Avenue with all great entertainment, eclectic shopping and restaurants, live music, and more. The rental includes use of bikes and kayaks. Kayaks are kept at 998 Oxford Dr. We are available to launch or to help you launch kayaks at a local spot. Front porch pictured is part of the main house and is use of this space is not included.

Guesthouse in Downtown Sarasota

4.97 out of 5 average rating, 438 reviews

Quick and Easy Walk Downtown - Tons of Amenities

Are you coming to Sarasota on vacation or perhaps considering moving here? If yes, then the Carriage House is the perfect place to use as a base camp while you explore the area and experience the best Sarasota has to offer. Quick and easy walk to dozens of casual restaurants, cool bars and unique shops. 5 minutes to Selby Gardens. 10 minutes to the Sarasota Bayfront. Main street is half a mile away. We provide tons of amenities including bikes, kayaks, beach chairs and umbrella.

Townhouse in Sarasota

4.77 out of 5 average rating, 131 reviews

Peaceful Oasis: King Bed & Incredible Views

You have arrived, upon entering you will go upstairs to your spacious duplex. You will be greeted by an amazing view of the intercoastal waterway. You will love kayaking on the waterway & seeing all the amazing wildlife. You can sit on your downstairs patio with a cup of coffee or you can take a stroll to Turtle Beach & enjoy the sunset. Hop aboard the trolley & go to the Village & eat and drink at one of our famous restaurants or one of our favorite hot spots. See Guidebook.

Vacation home in Venice

4.83 out of 5 average rating, 125 reviews

🌟Venice Cute Pool Villa with bikes Kayaks 🌈🐬

Escape to our charming Venice pool home, where relaxation meets adventure! Perfectly located near the water, this tranquil three-bedroom retreat is nestled on a quiet, palm-lined street. Enjoy easy access to bikes and kayaks for exploring, plus all the beach essentials: cooler, umbrella, and chairs. The pool awaits for sunny days and peaceful evenings (note: a brand-new pool cage is on its way, expected in December). Book now to experience Venice’s beauty from your private oasis!

Townhouse in Ruskin

4.93 out of 5 average rating, 213 reviews

Waterfront Townhome w/ Heated Pool & Balconies

Relaxation awaits you the moment you step in to Bahia Bungalow, a 2 Bedroom, 1.5 Bath town home nestled in Little Harbor Resort. Little Harbor is located on a partially private guest reserved beach in Ruskin, a short drive from Tampa, Sarasota & St. Pete. The resort overlooks Tampa Bay & features a heated outdoor pool, basketball and pickleball courts, fitness area, a playground & a marina. Dining within the Resort include a bay-view restaurant, a poolside bar/grill.

Home in Anna Maria

4.94 out of 5 average rating, 167 reviews

Re-Modeled & Now Ready for Post-Hurricane Visits!

* It doesn't get much better than being right on the water, located on a wide canal, and ½ block from the beach. * Enjoy the large 16' x 30' private pool in a picturesque tropical landscape along with a 30' fishing/boat dock. * Within walking distance of Pine Avenue, City Pier, Two Scoops, Waterfront Restaurant, Galati's Marina, and Island Ocean Star Restaurant. *Less than a 3 minute walk to Bay Beach and a 15 minute walk to Bean Point.

Home in St. Petersburg

4.83 out of 5 average rating, 214 reviews

Bungalow near the sea

Welcome to our bungalow by the sea It is just 3 blocks away from waterfront Lassing Park, which can be enjoyed with kayaks and bicycles that are available for free, and perfect for exploring nearby downtown Saint Petersburg and the pier. The house is completely furnished with everything you need for a great stay. Charcoal grill, TV, coffee, Ironing board and iron , Wi-Fi Internet and Beach toys So kick back and relax and enjoy your stay.

Vacation rentals for every style

Get the amount of space that is right for you

Villas

Luxurious estates for the ultimate escape

Apartments

Convenient locations with everyday essentials

Bungalows

Intimate homes. inviting architecture

Popular amenities for Sarasota kayak rentals

Free parking on premises

Air conditioning

House rentals with a kayak

Home in Venice

4.91 out of 5 average rating, 32 reviews

Venice Pool + Hot Tub Oasis (2 bed/2bath)

Home in Holmes Beach

4.93 out of 5 average rating, 41 reviews

Backyard Bliss Anna Maria Island

Home in Bradenton

4.95 out of 5 average rating, 128 reviews

Historic Wares Creek 3 bedroom with dock access

Home in Apollo Beach

4.98 out of 5 average rating, 123 reviews

5 Bed/4 Bath Waterfront "Lay Low" in Apollo Beach

Home in North Port

4.99 out of 5 average rating, 84 reviews

North Port -Nov/Dec Available - Fish/Canoe/Bike

Home in Bradenton

4.93 out of 5 average rating, 54 reviews

Waterfront w/ Pool, Dock + Paddle/Kayaks | Sea Gem

Home in Sarasota

5 out of 5 average rating, 13 reviews

Beautiful MidCentury Modern Home

Home in Bradenton

4.94 out of 5 average rating, 158 reviews

4/2 house/pool we have power/wifi/water IMG blake

Cottage rentals with a kayak

Cottage in Pass-a-Grille Beach

4.8 out of 5 average rating, 254 reviews

Sunny PaG Island rental w/bikes-just steps2beach

Cottage in Holmes Beach

5 out of 5 average rating, 5 reviews

Anna Maria Cottage w/Golf Cart

Cottage in Englewood

4.89 out of 5 average rating, 116 reviews

Free kayak/bikes/walk to beach/full cottage #1

Cottage in Englewood

5 out of 5 average rating, 23 reviews

The Coastal Oasis. Only 8 minutes from the Beach!

Cottage in Placida

4.98 out of 5 average rating, 41 reviews

Escape to a Hidden Gem, Beach Cottage on LGI

Cottage in Englewood

4.89 out of 5 average rating, 167 reviews

Free Kayaks! Waterfall Pool! Beach! am

Cottage in Holmes Beach

5 out of 5 average rating, 5 reviews

Steps To The Beach, Private & Heated Pool, Renovat

Cottage in Sarasota

4.96 out of 5 average rating, 74 reviews

Cottage by the Bay - free Level 2 EV charging

Cabin rentals with a kayak

Cabin in Port Charlotte

4.97 out of 5 average rating, 29 reviews

Unique loft experience for motorcycle enthusiasts

Cabin in Arcadia

5 out of 5 average rating, 40 reviews

Waterfront Retreat- w/Kayaks & Peace River access

Cabin in Ruskin

4.75 out of 5 average rating, 4 reviews

River Cabin Million Dollar View! New Management!

Cabin in Arcadia

5 out of 5 average rating, 13 reviews

Riverfront Cabin W/ Kayaks

Quick stats about vacation rentals with a kayak in Sarasota

Total rentals
50 properties
Nightly prices starting at
$40 before taxes and fees
Total number of reviews
2K reviews
Family-friendly rentals
30 properties are a good fit for families
Pet-friendly rentals
30 properties allow pets
Rentals with a pool
20 properties have a pool

Destinations to explore